A Three-day Weekend in Northampton, MA

By Lynn Davis Post > Back to Blog 

What are you doing October 6, 7 & 8?

Deep in the heart of the Connecticut River Valley, surrounded by the gently rolling foothills of the Green Mountains and the Berkshires, lies Northampton, the hometown of the Paradise City Arts Festival. Come autumn, the hills turn brilliant shades of red and gold, a cornucopia of apples, pears and pumpkins appear on every farm stand, the air turns crisp, and bustling Northampton becomes home to hundreds of the country’s most celebrated artists and makers.

New England’s most uncommon destination, Northampton will surprise you with its sophistication, diversity and eclectic flavor, small-town ambiance and big-city features. Check out this guide to plan a getaway to Northampton this fall.
Hotel Northampton

Historic Hotel Northampton, One of Many Lodging Choices

Friday Night

Northampton is eminently accessible with a two-hour (or less) drive from Boston, Connecticut, Rhode Island, and southern New Hampshire, and a three-hour drive from New York City, Burlington, VT and Portland, ME. Or, did you know you can take the Amtrak Vermonter from NYC to Northampton? The station is walking distance from both downtown and the Paradise City Arts Festival.

For lodging, you can choose from historic hotels and inns, motels and quaint bed & breakfasts, scattered up and down the Pioneer Valley in Northampton, Hadley or Amherst. Convenient to many of the Valley’s attractions, most are within a few miles of the Festival.

Once you get settled in your room, drive or walk downtown and choose among an abundance of great restaurants. From India House (Indian), to Spoleto (Italian) to the relaxed and casual Eastside Grill (where New England meets New Orleans!), you’ll certainly dine well. Check out more suggestions here or for a complete list of all eateries in the area, click here.

Saturday: The Main Event – Paradise City Arts Festival


Stephanie Young. Calmwater Designs, and her Porcelain Art Nouveau-Inspired Ceramics

The Paradise City Arts Festival is the main event happening on the long weekend of October 7, 8, & 9.  Paradise City presents almost 250 carefully curated artists and makers from across America plus lively music, great food from local restaurants, and special demonstrations. This sprawling, thrilling showcase for the arts is an experience like no other – beautiful, unique, festive, and fun. With so much to see, you just may want to go back a second day.

Saturday Night

Northampton and environs are a foodie’s paradise.  What’s your favorite cuisine?  Alina’s right over the bridge in Hadley serves delicious Italian food …  The Sierra Grill downtown serves a full menu of creative small plates and lamb, duck, chicken, and beef entries for which you can choose a variety of sauces. Northampton boasts a good half dozen sushi restaurants too.

Northampton is also home to theaters, music halls and clubs, and the five local colleges keep the atmosphere lively. The Academy of Music Theater is a historic venue for live theater, dance, film, music, and arts education. Check out their calendar for listings. The Iron Horse Music Hall and many local bars, restaurants, and nightclubs have live performances on weekend nights. Indeed, classic blues guitarist Albert Cummings is on stage Saturday, October 7 at the Iron Horse.


You’ll have a wide choice of regional bakeries and breakfast spots on Sunday morning.  Jakes just off Main Street provides “great food, cozy atmosphere, local and organic ingredients.”  Sylvester’s, on Pleasant Street, is known for its copious and inventive brunches. A variety of cafes and local bakeries compete to serve the best coffee, pastries, bagels, and sandwiches.

After your fortification, head back to Paradise City at the Three County Fairgrounds. Perhaps you found a favorite item on Saturday ‒ a photograph, earrings, ceramics, scarf, or what have you. After pondering your acquisition, you’re ready to return and buy.

The Connecticut River Valley as viewed from Mount Sugarloaf

By Sunday afternoon, you may want to get out and do something active.  Drive about 10 miles north to South Deerfield, MA at 1-91 exit 24.  Then climb or drive to the top of Mount Sugarloaf for a spectacular view of the Connecticut River that has inspired artists for nearly 200 years. Watch the sun light up the stunning fall color and then set into the Connecticut River Valley.

Colonial Dining Room at The Farm Table Restaurant

Feeling a little righteous for having hiked in the afternoon, you can pick a bar and try one or more of the craft cocktails available at local restaurants and curated by our Paradise City Arts directors. The delightful Farm Table Restaurant, another 15 miles north from Mount Sugarloaf, serves a varied cuisine of locally-sourced foods with rustic charm.  Their signature craft cocktail is the Blackberry Jam Martini which incorporates a distinctive artisanal blackberry jam as well as Tito’s Vodka, Chambord, Fresh Lemon and Lime juice.


Fall Color at the Botanic Garden of Smith College

On Monday, if you still have time for more fun, visit the Botanic Garden of Smith College for a riot of fall color highlighting Japanese maples, paperbark maples, tupelo trees, red maples and more.

The Vermonter whisks you back to NYC in just over four hours. Or, take an easy drive back to Boston, Connecticut, New Hampshire, or Vermont.  It’s all in a day’s fun! You’ll have experienced a vacation to a sophisticated cultural city, a world-class arts festival, the rolling mountains of western Massachusetts, and downtown Americana all rolled into one.