New England is a vacation paradise known for its historical attractions, beautiful wilderness, and culinary prowess. Across such a vast region with an extensive amount of attractions to explore, it can be difficult to choose where to go.
That’s why we’ve created a full itinerary (from southwest to northeast) of the best things to do, dining spots, and places to stay across the region. You’ll find two to three days’ worth of attractions in each city, town, or state to plan multiple weekend getaways in New England, or string them together for the ultimate New England experience.
Connecticut’s Waterfront Towns & State Parks
3-hour, 45-minute drive to Brewster Cape Cod
Travelers often overlook Connecticut, missing out on an authentic New England experience with fewer crowds than other states in the region. Since the state was one of the original 13 colonies, it’s home to some of the oldest towns and cities in the country.
For our getaway itinerary, though, we’re going to focus on the waterfront locations along the Long Island Sound — a picturesque stretch of shoreline with excellent state parks — while staying in Connecticut.
Best Things to Do in Connecticut
Stamford Connecticut
With a lively downtown atmosphere, Stamford is growing with fantastic shopping and dining options. It also has several recreational spots, such as the Stamford Museum & Nature Center that features more than 80 acres of nature trails and a permanent museum collection of more than 20,000 items.
Silver Sands State Park
Comprising more than 300 parcels of land, Silver Sands State Park in Milford has a beautiful, three-quarter-mile boardwalk and opportunities for saltwater fishing and swimming.
New Haven Connecticut
Famous for Yale University, New Haven has pretty parks to explore and impressive buildings to gawk at on the campus. Additionally, it’s home to part of West Rock Ridge State Park, featuring hiking, mountain biking, fishing, car-top boating, horseback riding, and picnicking.
NEARBY: Sleeping Giant State Park in Hamden Connecticut offers hiking, a lookout tower, stream fishing, and picnicking too.
Hammonasset Beach State Park
At Hammonasset Beach State Park in Madison, you’ll find more than 2 miles of beach — the biggest public beach park in the state — for strolling and saltwater swimming. You can go car-top boating, camping, bicycling, and hiking at the park, as well as visit the Meigs Point Nature Center.
Gillette Castle State Park
In East Haddam, Gillette Castle State Park is home to a 184-acre estate. The focal point is the 24-room Gillette Castle — a mansion reminiscent of a medieval fortress built from the creative genius of William Hooker Gillette from 1914 to 1919. Also within the park are opportunities for hiking, river camping, and picnicking.
Stonington Connecticut
Founded in 1662, Stonington is the state’s oldest settlement and worth visiting for a peaceful day trip. Within it, the shoreside Village of Mystic is reminiscent of the town’s rich maritime history.
Restaurants on a Connecticut Getaway
Across this shoreline of Connecticut are numerous delicious places to eat. Here are a few of our top picks near each of the above attractions:
- Cafe Silvium in Stamford — old-world Southern Italian food and wine
- Nautilus near Silver Sands State Park— American fare, specialty cocktails, and wine
- TOKA Asian Kitchen in New Haven — Asian fusion cuisine with fresh ingredients, beer, sake, and wine
- Pho Madison near Hammonasset Beach State Park — authentic, from-scratch Vietnamese cuisine and bubble tea
- The Village Bistro in Gillette Castle State Park — New American cuisine with European flair
- Sift Bake Shop Mystic in Stonington — French bakery with a bit of everything
Madison Connecticut Lodging
Staying in Madison means that these coastal Connecticut attractions are only about a 1-hour drive away. The Homestead Madison is a welcoming boutique hotel experience with an intimate bed-and-breakfast atmosphere.
History & Recreation in Newport Rhode Island
1-hour, 30-minute drive to Brewster Cape Cod
A peninsula on an island in Rhode Island, Newport is considered the hub of The Classic Coast — alongside eight other coastal communities. The city has all the makings of a fantastic New England getaway destination, particularly its historical and natural attractions.
Top Attractions in Newport
Mansion Tours
Some of America’s wealthiest individuals and families made Newport their summer residence during the Gilded Age, building extravagant mansions that have been meticulously maintained over the years.
From the first home with electricity to a 70-room Italian Renaissance palazzo, there are over a dozen mansions to tour — such as the 1892 Marble House, 1895 The Breakers, and 1901 The Elms.
Rough Point Museum
The home of Doris Duke — heiress, philanthropist, and collector — the now Rough Point Museum is a mansion full of her legacy of fashion collections and decorative and fine arts. There are panoramic views of the Atlantic as well.
Cliff Walk
For more views of the water, stroll along the world-famous Cliff Walk on the southeast shoreline of the city. The 3.5-mile trail consists of five main sections, each with its own entry and exit. Benches, public restrooms, and water stations are available along the way.
State Parks Along Ocean Drive
Featuring 10 miles of shoreline, the iconic Ocean Drive is a scenic road that passes some of Newport’s nansions and several other points of interest — such as Brenton Point State Park and Fort Adams State Park.
Bowen’s Wharf
Enjoy a seaside view while you shop and dine in Newport at Bowen’s Wharf — the Anchor of the Newport Waterfront. Some popular shops include Primavera and Anchor Toffee, while Luke’s Lobster and 22 Bowen’s Wine Bar & Grille are a couple of favorite dining haunts.
More Newport Restaurants
You’ll find tons of restaurants around Newport Rhode Island outside of Bowen’s Wharf. Here are a few standout locales:
- Kellie’s Cafe — traditional American and British breakfasts, sandwiches, and pastries
- Humming Bird — authentic Jamaican cuisine made with seasonal, fresh ingredients
- Jo’s American Bistro — award-winning burgers, lobster salad rolls, and gluten-friendly dishes
Lodging in Newport
There are a couple of great places to stay in Newport. Hydrangea House Inn Bed & Breakfast is a historic 1856 Victorian mansion with modern comforts that don’t impede on the historic charm. The Francis Malbone House Inn is a waterfront property dating back to the 18th century with Georgian architecture and sophistication.
Providence Rhode Island’s Art, Entertainment, & Italian
1-hour, 30-minute drive to Brewster Cape Cod
Founded in 1636, Providence Rhode Island is one of the oldest cities in New England and is the state capital. The Providence River runs through the center, giving it the feeling of a European city.
Along with historical buildings and landmarks, the city is a haven for art, entertainment, and Italian cuisine — making it one of the best getaways in New England.
Best Things to Do in Providence
Rhode Island School of Design Museum of Art
Since 1877, the RISD Museum has been a vibrant part of this creative community, displaying artwork that represents diverse ancient cultures. The collection features over 100,000 pieces of art and design — decorative arts, costumes and textiles, furniture, paintings, and sculptures.
Providence Performing Arts Center
To see a theatrical show, head to the Providence Performing Arts Center. Some of the biggest names in music, comedy, and culture perform here, and it hosts some of the top national Broadway tours.
Waterplace Park & Riverwalk
An essential part of Providence’s history, Waterplace Park was once the Great Salt Cove and covered with water. The water drained over time, and a railroad ran through the area by 1898. In the 1980s and ’90s, though, this city center was rejuvenated and is now home to concerts, restaurants, and a riverwalk.
Roger Williams Park Zoo
Amid 40 acres, the Roger Williams Park Zoo is home to over 160 species of animals — including the only Komodo dragon in New England and animal encounters. Some species are over 1 million years old. In addition to the animals, there’s a zip line and fun events throughout the year.
Rhode Island State House
On the historic side of attractions, the Rhode Island State House was built between 1895 and 1904. You can go on guided and self-guided tours and stop by the visitor center and gift shop for some memorabilia.
Historic Federal Hill
Along Atwells Avenue, Historic Federal Hill is the ideal place for shopping and dining in Providence. Get vintage items at Rocket to Mars and everything to make authentic Italian at Venda Ravioli. Or, dine on some of the best Italian dishes in the world at Camille’s and Saint Federal Hill.
More Providence Restaurants
There are many more restaurants in Providence outside of Historic Federal Hill. Check out these local favorites:
- The Coffee Cup — hot and cold coffees and teas, sandwiches, soups, salads, and pastries
- Livi’s Pockets — Middle Eastern cuisine
- Res American Bistro — brunch and lunch dishes
- Dune Brothers Seafood — seafood favorites
- Bayberry Garden — brunch, lunch, and dinner with a raw bar and cocktails
Providence Lodging
The Christopher Dodge House is a renovated 1858 Italianate mansion full of charm and original design. Stay in one of its 14 rooms, and savor the daily complimentary hot breakfast and early and afternoon tea.
Vast Landscapes & Culture on Cape Cod Massachusetts
With more than 550 miles of coastline, Cape Cod has some of the most premier beaches in New England. There’s natural beauty at every turn, offering lots of recreational activities. The Cape offers several cultural attractions too. If you’re only here for a few days, you don’t want to miss these attractions.
Top Attractions on Cape Cod
Heritage Museums & Gardens
Suitable for visitors of all ages, Heritage Museums & Gardens in Sandwich features over 100 acres of amazing gardens and museum exhibits, as well as a vintage, hand-carved carousel. During the holidays, Heritage hosts Gardens Aglow with tens of thousands of lights and themed displays.
Cape Cod Rail Trail or Old King’s Highway
If you enjoy walking, biking, rollerblading, or horseback riding, the CCRT is a 25-mile paved trail that passes through several of the Cape’s towns. On the other hand, you could take a scenic drive through 11 towns via Old King’s Highway — aka Route 6A.
Cape Cod National Seashore
With 40 miles of coastline, the Cape Cod National Seashore is a recreation paradise. You can go hiking, biking, beachcombing, swimming, and lighthouse viewing across this protected land. Stop at the Salt Pond Visitor Center for exhibits and information about exploring the park.
Wellfleet Drive-In & Cinemas
Throughout the summer, the Wellfleet Drive-In Theatre is the place to go for watching double features outdoors every night. It offers the quintessential experience with a Snack Bar.
Also on the property is an indoor cinema that’s open all year, Dairy Bar & Mini Golf, and Flea Market — the biggest on the Cape.
Pilgrim Monument & Provincetown Museum
Head to Provincetown Cape Cod to learn about town and Cape culture and history at the Pilgrim Monument & Provincetown Museum. The monument towers over the town at 252 feet — the tallest structure made of all granite in the country — and you can climb to the top for the ultimate view.
Cape Cod Getaway Restaurants
Aside from charm and stunning beauty, Cape Cod is known for being a culinary wonderland. From some of the freshest seafood on the East Coast to international cuisines, here are some of the best Cape restaurants for dining during your visit:
- The Edge – Thick Square Pizza near Heritage — thick rectangular shaped pizza
- Keltic Kitchen near CCRT in West Yarmouth — Irish breakfast and lunch dishes
- Spinnaker along Route 6A in Brewster — Mediterranean-chic boutique restaurant
- The Lobster Pot near Pilgrim Monument — high-quality lobster dinners and rolls
Lodging on Cape Cod
Rated the #1 Bed and Breakfast in the U.S. on Tripadvisor, Candleberry Inn is located in Brewster Cape Cod, making it a central location to explore the region. We have guest rooms, suites, and cottages to choose from and serve a fresh, homemade breakfast every morning.
When you start to plan your New England getaway, check our availability for your travel dates.
Boston Massachusetts’ Abundance of History
1-hour, 30-minute drive from Brewster Cape Cod
As the birthplace of the American Revolution and the capital of Massachusetts, Boston is chock full of historical sites. They’re practically around every corner and mixed with a few natural attractions and shopping spots. Which ones should you check out then?
Best Things to Do in Boston
John F. Kennedy Presidential Library and Museum
One historical site that history buffs will drool over is the John F. Kennedy Presidential Library and Museum. This excellent museum houses details about the 35th president’s life, including presidential papers, recreations of his Oval Office desk, and other Kennedy-related memorabilia.
Boston Tea Party Ships & Museum
At the Boston Tea Party Ships & Museum on Griffin’s Wharf, you get a hands-on look at one of the pivotal moments in Boston’s past. Climb aboard replica ships, discuss Colonial issues with period actors, and throw tea overboard (fake tea, of course).
Boston Common
From a cow pasture in the mid-1600s to the oldest public park in the United States, Boston Common is a focal point in the city for musical and theatrical performances and other events all year. The park is great for taking a casual stroll, playing yard games, picnicking when it’s warm, and ice skating when it’s cold.
Plus, it’s the starting point for the Freedom Trail, a 2.5-mile path that weaves through the most historic sites in Boston — including the Faneuil Hall Marketplace & Quincy Market, New England Holocaust Memorial, and Paul Revere House.
Boston Public Garden
Despite being next to Boston Common, the Boston Public Garden is a very different space. Established in 1837, it was the first public botanical garden in the country and is beautifully organized with colorful flowers and exotic trees. It’s a breathtaking sight that you don’t want to miss.
Newbury Street
Home to magnificent 19th-century brownstone houses, Newbury Street is more than architecture. It’s the best spot in Boston for dining and shopping. Check out the goods at L.A. Burdick Handmade Chocolates and Byredo, and grab a bite at Jonquils Cafe and Bakery and Redwhite Boneless Ramen.
Restaurants in Boston
Aside from Newbury Street, Boston has plenty more restaurants. Here are a few that we recommend near or in the North End:
- Bonne Chance Cafe — Korean cuisine, cold and hot sandwiches, wraps, coffee, and more
- Mo’Rockin Fusion — traditional Moroccan food with a twist
- Kala Thai Cookery — fine Thai cuisine
- Lily’s Bar Pizza Patio — club-like pub with signature artisan pizza and local beer
- Mamma Maria — nationally acclaimed Italian restaurant
Boston Lodging
There are a couple of standout bed and breakfasts in Boston Massachusetts. Boston Yacht Haven is a world-class lodging option with 10 deluxe guest rooms, including a penthouse with a view of the city and harbor. Clarendon Square is a historic inn with some of the finest luxury accommodations in Boston and a rooftop hot tub.
Nature & Scenic Views Galore in Vermont
4-hour, 30-minute drive from Brewster Cape Cod
When it comes to scenic vistas, Vermont makes for one of the best getaways in New England. It’s like one huge postcard filled with striking landscapes that beg to be photographed.
No matter when you visit, you will see beautiful scenery — flora in bloom during spring and summer, colorful leaves during fall, and snowfall during winter — and can enjoy recreational activities aplenty.
Top Attractions in Vermont
Quechee Gorge
One of the best Vermont destinations for a view is Quechee State Park. It’s home to Quechee Gorge, which is nicknamed Vermont’s Grand Canyon. Formed 13,000 years ago by glacial action, the gorge is 165 feet deep.
The Quechee Gorge Trail offers views of the gorge and the Ottauquechee River, which flows through the gorge and offers opportunities for fishing and whitewater rafting.
Woodstock Vermont
Considered one of America’s prettiest small towns, Woodstock is a charming, sleepy, and quaint place to visit. From Sugarbush Farm and Bourdon Maple Farm to the boutique and galleries to nostalgic covered bridges, it’s easy to spend a full day exploring Woodstock.
Killington Resort
At Killington Resort, you can experience activities all year — downhill mountain biking, golfing, scenic gondola rides, and ATV tours when it’s warm and skiing and snowboarding when it snows. You can even book a vacation package to play, stay, and dine at the resort.
Stowe Vermont
The Town of Stowe is another place that’s busy all year. Art shows and festivals are held through the summer, while skiing and snow sports are popular through winter.
Walk, bike, jog, skate, or cross-country ski the 5.5-mile paved Recreation Path from the village to Topnotch Meadow. From late fall through mid-April, the Mountain Road Shuttle stops at popular sites in the main and lower villages, as well as travels to the base of Mount Mansfield.
FACT: Stowe was the home of the von Trapp family (the same family from “The Sound of Music” film) after they left Austria during WWII.
Additionally, Stowe is home to Smugglers’ Notch State Park, which features the namesake narrow passage through the Green Mountains that’s lined with 1,000-foot cliffs.
The road was a means for trading goods with Canada through the 1800s despite the practice being made illegal with an embargo act. Later, it was used to help slaves escape to Canada and then during Prohibition to smuggle liquor from Canada.
Additionally, the park offers lots of hiking and mountain biking trails, bouldering, ice climbing, cave exploring, and picnicking. For the full Stowe and state park experience, you could play, stay, and dine at Smugglers’ Notch Resort.
Shelburne Vermont
Established in 1763 along Lake Champlain, Shelburne is a quiet town about 7 miles south of the state’s largest city — Burlington. During your visit, enjoy water sports on the lake (weather permitting), tour the famous Vermont Teddy Bear Company (a staple since 1981) and explore impressive indoor and outdoor exhibits at Shelburne Museum.
Vermont Getaway Restaurants
Aside from the restaurants at Vermont’s resorts, there are several dining options near each of these attractions. This list will get you started:
- Foley Brothers Beer Garden near Quechee Gorge — pub fare and local brews
- The Prince & The Pauper Restaurant in Woodstock — excellent fine dining
- Grant’s in Stowe — upscale comfort food and specialty cocktails
- Cucina Antica in Shelburne — family-friendly bistro with mouth-watering pizza
Lodging in Warren Vermont
Staying in Warren allows you to reach the above Vermont attractions in about 1 hour or less. West Hill House Bed & Breakfast is a historic 1850s farmhouse turned retreat with modern conveniences and solar power near recreational activities in the Mad River Valley.
New Hampshire’s Mix of Nature & History
3-hour drive from Brewster Cape Cod
Between the charming and historic cities and towns, New Hampshire is full of astounding natural beauty, offering a bit of everything for all ages and interests.
There are numerous historic sites and cultural landmarks, some of which are the oldest in the country, while outdoor adventures await — such as hiking, kayaking, camping, and skiing.
Best Things to Do in New Hampshire
Monadnock State Park
Featuring a namesake 3,165-foot peak, Monadnock State Park features thousands of acres of protected lands. This National Natural Landmark has hours of hiking and two campgrounds. The mountain-top views are especially breathtaking during fall foliage.
Manchester & Concord New Hampshire
Since Manchester and Concord are less than a 30-minute drive apart, it’s possible to fit them both into a day trip. They’re located in the Merrimack Valley and often overlooked but offer two different experiences.
While Concord is the smaller city, it’s the state capital and features a magnificent State House, the New Hampshire Historical Society, and a planetarium at the McAuliffe-Shepard Discovery Center. Manchester is the larger city and maintains its industrial heritage — centered around its monolithic riverside mills, some of which have been converted into condos and shops.
Mount Washington State Park
With more than 60 acres, Mount Washington State Park is located at 6,288 feet on the highest summit in the Northeast. The view from the peak extends to Maine, Vermont, Massachusetts, New York, and beyond on a clear day. Some things to do include the Tip Top House Historic Site, The Mount Washington Cog Railway, and the Mt. Washington Auto Road.
White Mountain National Forest
An expansive 750,000 acres surrounding Mount Washington State Park, the White Mountain National Forest is one of the most popular attractions in New Hampshire.
The forest has it all — mountain lakes and streams, Alpine peaks, hardwood forests, and wildlife. Plus, there are tons of recreational opportunities — hiking trails (including the Appalachian Trail), snowmobile trails, skiing areas, and campgrounds.
Lake Winnipesaukee
Head to Lake Winnipesaukee for even more recreation — beachfront swimming, boating, fishing, hiking and biking, and cross-country skiing. You can even cruise the lake and around the many islands on a boat tour that includes some history of the lake and amazing views.
Portsmouth New Hampshire
Founded in 1623, Portsmouth is a quintessential port town with islands of its own. You can tour the water and islands with Portsmouth Harbor Cruises and the Strawbery Banke Museum — a living history museum that takes you on a journey through time.
Restaurants on a New Hampshire Getaway
You’ll find delicious restaurants throughout the cities and small towns of New Hampshire. To narrow down your choices near the aforementioned attractions, check out these locales:
- Kimball Farm Jaffrey near Monadnock State Park — local seafood and homemade ice cream
- North End Bistro in Manchester — traditional Italian and American dishes
- Red Fox Bar and Grille near White Mountains — authentic wood-fire grilled pizza and more with gluten-free options
- Pavilion along Lake Winnipesaukee — seasonally inspired American dishes with vegan and gluten-free options
- Ristorante Massimo in Portsmouth — authentic, world-class Italian fare
Sanbornton New Hampshire Lodging
Since you’ll be traversing a lot of mountainous terrain around New Hampshire, it can take up to 2 hours to reach some of the above attractions from Sanbornton, but this is the most central spot. The Lake House at Ferry Point is a bed and breakfast in a 200-year-old house on Lake Winnisquam.
Quaint Coastal Towns & Vast Wilderness in Maine
4-hour drive from Brewster Cape Cod
The laid-back atmosphere and untouched nature across Maine makes the state a must-visit New England destination. With so much to see and do, it can be overwhelming to decide which places to visit. To make the most of your getaway, here are some top places to add to your itinerary.
Top Attractions in Maine
Southern Maine Coast Towns
The Southern Maine Coast is one of the most visited regions of the state because it’s full of charming towns. In York Maine, you’ll find beaches, golf courses, the famed Sohier Park & Nubble Lighthouse, and Mount Agamenticus.
Kennebunkport has beaches and historic sites, such as St. Ann’s Church and First Families Kennebunkport Museum, and Seashore Trolley Museum, as well as scenic sailing charters and whale watching tours.
With 7 miles of sand, Old Orchard Beach is the ultimate waterfront town. Plus, it’s home to The Pier for shopping and dining and Palace Playland for roller coasters and carnival games.
Sugarloaf Mountain & Ski Resort
A gorgeous backdrop for a getaway in New England, Sugarloaf Mountain is a retreat all year. Summer brings hiking, kayaking, zip lining, and scenic lift rides, while winter brings traditional downhill and Nordic skiing and fat-tire biking. And, the Sugarloaf Ski Resort offers all of this and more.
Mid Coast Maine Towns
A popular summer home region for New England residents, Mid Coast Maine maintains the charm for which the state is known. In Rockland, you can attend the Maine Lobster Festival, visit the Rockland Breakwater Lighthouse and Project Puffin Visitor Center, and book boat cruises.
Camden Maine is the ideal place for enjoying nature at Camden Hills State Park, festivals and events, and lighthouse harbor tours, as well as downtown shopping. Meanwhile, Belfast is the ideal place for city parks and trails — such as Belfast City Park, Heritage Park, the Harbor Walk, and the Belfast Rail Trail.
Bar Harbor & Acadia National Park
For good reason, two of the most famous and visited areas of Maine are Bar Harbor and Acadia National Park. The city is known as the gateway to the park with dining, shopping, and lodging just outside of its boundaries. The park offers hiking, lake activities, camping, scenic drives, and stargazing.
Baxter State Park
Located in the Maine Highlands, Baxter State Park is the ultimate wilderness haven. It features over 200,000 acres of hiking, fishing, swimming and other water activities, picnicking, wildlife viewing, and several overlooks of scenic vistas. Summer and winter camping are permitted and ideal for adventurers who like to rough it.
Maine Getaway Restaurants
Considered the Lobster Capital of the World, you can’t visit Maine without sinking your teeth into some of the freshest, tastiest lobster you’ll ever have. Many restaurants have other excellent culinary talents too. Here are a few to consider:
- Paloma’s Restaurant in Old Orchard Beach — American breakfast and lunch fare, including lobster rolls
- Coplin near Sugarloaf Mountain — seasonal dishes made with Maine ingredients and signature cocktails
- Franny’s Bistro in Camden — Southern favorites, French classics, and Italian seafood specialties
- The Barnacle in Bar Harbor — seafood at its best, including lobster rolls, with beer and unique cocktails
- Sawmill Bar & Grill near Baxter State Park — creative American dishes and spirits
Lodging in Boothbay Harbor Maine
A destination in itself, Boothbay Harbor is within a 3-hour drive of the above Maine attractions. Topside Inn is a retreat with harbor views, elaborate breakfasts and lunches, a relaxing environment, and stylish rooms and suites.
Start Planning Your Getaway in New England Now
Every season is the perfect season to plan getaways in New England. It’s an endlessly beautiful region with things to do and see all year.
And while you’re on Cape Cod, we at Candleberry Inn are more than happy to help you plan your Cape experience. You can even download our free Vacation Guide for tons more recommendations of things to do on the Cape.